Sodium hydride → (E)-3-(1H-Indol-7-yl)acrylonitrile

HRID 1198535

Reaktionsgleichung

Reaktionsgleichung von HRID 1198535
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[CH:23]=O)[CH:16]=[CH:15]1>O1CCCC1.C(OCC)(=O)C>[C:3](/[CH:5]=[CH:23]/[C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[NH:14][CH:15]=[CH:16]2)#[N:4]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2734629Indole-7-carboxaldehyde

Produkt 1

HCID 19959103(E)-3-(1H-Indol-7-yl)acrylonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride, 60% dispersion in mineral oil (0.10 g, 2.5 mmol) was added in portions over 10 minutes to a stirred solution of diethyl cyanomethylphosphonate (0.44 g, 2.5 mmol) in tetrahydrofuran (10 ml) cooled in ice. The mixture was stirred for 15 minutes then a solution of 7-indole carboxaldehyde (0.30 g, 2.1 mmol) in tetrahydrofuran (2 ml) was added dropwise. The mixture was stirred for 30 minutes, diluted with ethyl acetate, washed with water, dried and evaporated. The residue was chromatographed on silica in ethyl acetate-hexane (1:3) to give the product.

Aufarbeitung

  1. temperaturecooled in ice
  2. stirringThe mixture was stirred for 30 minutes
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica in ethyl acetate-hexane (1:3)
  7. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-f2671e47b7334dd69bded84396db529f
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281593

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